95: Ryan Holiday: The Obstacle is the Way

Ryan Holiday is a media strategist and prominent writer on strategy and business. After dropping out of college at 19 to apprentice under Robert Greene, author of The 48 Laws of Power, he went on to advise many bestselling authors and multiplatinum musicians. He served as director of marketing at American Apparel for many years, where his work was internationally known.

His campaigns have been used as case studies by Twitter, YouTube, and Google and written about in AdAge, the New York Times, Gawker and Fast Company. His first book, Trust Me I’m Lying: Confessions of a Media Manipulator–which the Financial Times called an “astonishing, disturbing book” was a debut bestseller and is now taught in colleges around the world. His subsequent books, Growth Hacker Marketing and The Obstacle is the Way were both published by Penguin/Portfolio.

Favorite Success Quote

“The impediment to action advances action. What stands in the way becomes the way.” – Marcus Aurelius

Key Points

1. If You Want a Great Mentor Be Humble 

Whenever young men go out looking for mentors, they often do so with a completely backward approach.

They go to their desired mentor and then flaunt their skills, pretending to be the greatest thing that this world has ever seen.

But there’s a problem.

Successful people do not want apprentices who have it all figured out.

They want someone who is humble.

Someone who is willing to learn and listen and take action.

That’s it.

If you want great mentors in your life, then drop the ego and be honest.

Tell them that you dont have the skills or the knowledge that they need, but you have the drive, the ambition, and the willingness to learn.

You would be surprised how often this attitude will open doors where there once stood only walls.

2. Be Willing to Just do the Work 

Whatever your goals, dreams, and ambitions are, you must be willing to just do the work.

That’s it.

If you want to be great, if you want to be remembered, if you want to be world class, then show up each and every day and do the work.

Want a 7-figure business? Then do the work.

Want a great body? Then do the work.

Want a beautiful wife and an amazing family? Then do the work.

3. Learn to Experience Situations through the Lens of Stoicism

In every situation, there are both positives and negatives.

The philosophy of stoicism doesn’t ignore or hide the negatives, rather it focuses on the positives.

In every situation, there is something to be grateful for and a lesson to be learned.

If you lost your job, now you have time to take a breath and reassess your goals and dreams while you work towards finding a new stream of income.

If your girlfriend cheats on you, then you have the ability to use this tragedy to figure out where it went wrong and how you can improve next time.

There is always a silver lining.

You just have to be willing to look for it.

4. Don’t Predicate Your Happiness on External Events 

If you want to experience more joy and happiness in your life, then you must remove your focus on external things.

True happiness comes from focusing entirely on things that are inside of your control.

Focus on your actions, your habits, and your mind and not the results that are happening in the outside world.

Just think about it.

If you are only happy when you are rich, what happens when there is a downturn in the market and your entire industry is flipped on its head?

But if you are happy whenever you are working hard towards the attainment of a more glorious goal then markets can rise and fall and your happiness will not change a beat.

5. Find What Fulfills You

At the end of the day, we only have one life on this planet.

And as such, it is important that we spend most of our time doing that which gives us joy and fills our spirit.

Life is too short to waste on an uninspiring vision.

Figure out what fulfills you and go do that.

Do you love to write? Play music? Build websites? Travel?

Figure out your passion, figure out what fulfills you, and then find a way to make it your life.

Influential Books

Meditations by Marcus Aurelius

Plutarch by Plutarch


Connect with Ryan Holiday


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